(2R,3S,4S,5R)-6-[(tert-butyldiphenylsilyl)oxy]-2,3,4,5-tetrahydroxyhexanal

• ChemBase ID: 139005
• Molecular Formular: C22H30O6Si
• Molecular Mass: 418.5555
• Monoisotopic Mass: 418.18116521
• SMILES: CC(C)(C)[Si](c1ccccc1)(c1ccccc1)OC[C@H]([C@@H]([C@@H]([C@H](C=O)O)O)O)O
• Canonical SMILES: O=C[C@@H]([C@H]([C@H]([C@@H](CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)O)O)O)O
• InChI: InChI=1S/C22H30O6Si/c1-22(2,3)29(16-10-6-4-7-11-16,17-12-8-5-9-13-17)28-15-19(25)21(27)20(26)18(24)14-23/h4-14,18-21,24-27H,15H2,1-3H3/t18-,19+,20+,21-/m0/s1
• InChIKey: BSEPYXNJJUUAEY-BQJUDKOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R)-6-[(tert-butyldiphenylsilyl)oxy]-2,3,4,5-tetrahydroxyhexanal
• IUPAC Traditional name: (2R,3S,4S,5R)-6-[(tert-butyldiphenylsilyl)oxy]-2,3,4,5-tetrahydroxyhexanal
• Synonyms: 6-O-(tert-Butyldiphenylsilyl)-D-galactal

Database IDs

• CAS Number: 137893-35-7
• MDL Number: MFCD01321372
• PubChem SID: 24871712; 162233256
• PubChem CID: 71310202

CALCULATED PROPERTIES

• Acid pKa: 11.802486
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.0147998
• LogD (pH = 7.4): 2.014783
• Log P: 2.0148
• Molar Refractivity: 106.5821 cm^3
• Polarizability: 44.52526 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: >113 °C; >235.4 °F
• Optical Rotation: [α]20/D +4°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: 97%
• Contains: ~5 wt. % ethyl acetate to induce mobility of syrup
• Empirical Formula (Hill Notation): C22H28O4Si

DETAILS

Sigma Aldrich - 480711

Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.1